KR20230162873A - Heterocyclic compound, organic light-emitting device and composition for organic material layer of organic light-emitting device comprising same - Google Patents

Abstract

The present specification provides a heterocyclic compound, an organic light-emitting device containing the same, and a composition for the organic material layer of the organic light-emitting device.

Description

Heterocyclic compound, organic light-emitting device containing the same, and composition for the organic material layer of the organic light-emitting device {HETEROCYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE AND COMPOSITION FOR ORGANIC MATERIAL LAYER OF ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME}

The present invention relates to heterocyclic compounds, organic light-emitting devices containing the same, and compositions for organic material layers of organic light-emitting devices.

Organic electroluminescent devices are a type of self-luminous display devices and have the advantage of a wide viewing angle, excellent contrast, and fast response speed.

Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then annihilate, emitting light. The organic thin film may be composed of a single layer or multiple layers, depending on need.

The material of the organic thin film may have a light-emitting function as needed. For example, as an organic thin film material, a compound that can independently form a light-emitting layer may be used, or a compound that can act as a host or dopant of a host-dopant-based light-emitting layer may be used. In addition, as a material for the organic thin film, compounds that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

In order to improve the performance, efficiency, and lifespan of organic light-emitting devices, the development of organic thin film materials is continuously required.

US Patent No. 4,356,429

The present invention seeks to provide a heterocyclic compound, an organic light-emitting device containing the same, and a composition for the organic material layer of the organic light-emitting device.

In an exemplary embodiment of the present application, a heterocyclic compound represented by the following formula (1) is provided.

[Formula 1]

In Formula 1,

Et is a substituted or unsubstituted heteroaryl group containing N of C2 to C60,

Ar1 is a substituted or unsubstituted aryl group of C6 to C60; A substituted or unsubstituted C5 to C60 polycyclic heteroaryl group; or a substituted or unsubstituted amine group, p is an integer of 1 to 4, and when p is 2 or more, the substituents in parentheses are the same or different from each other,

L1 and L2 are the same or different from each other and are each independently directly bonded; or a substituted or unsubstituted C6 to C60 arylene group, m and n are each an integer of 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same or different from each other,

R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

Two or more groups among R1 to R3 that are adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Or, it forms a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring.

Additionally, in an exemplary embodiment of the present application, a first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a heterocyclic compound represented by Formula 1. provides.

In addition, in an exemplary embodiment of the present application, an organic light-emitting device is provided wherein the organic material layer further includes a compound represented by the following formula (2).

[Formula 2]

In Formula 2,

Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted heteroaryl group of C2 to C60, q and r are each integers of 1 to 4, and when q and r are each 2 or more, the substituents in parentheses are the same or different from each other,

L3 is a direct bond; Substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted heteroarylene group of C2 to C60, o is each an integer of 0 to 3, and when o is 2 or more, the substituents in parentheses are the same or different from each other,

Ra and Rb are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group,

R9 and R10 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A substituted or unsubstituted C2 to C60 heteroaryl group,

g is an integer from 0 to 5, h is an integer from 0 to 4, and when g and h are each 2 or more, the substituents in parentheses are the same or different from each other.

Lastly, in an exemplary embodiment of the present application, a heterocyclic compound represented by Formula 1; and a composition for the organic material layer of an organic light-emitting device comprising the compound represented by Formula 2 above.

The heterocyclic compounds described herein can be used as organic layer materials for organic light-emitting devices. In other words, it can serve as a light emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc. in an organic light emitting device. In particular, it can be used as a light-emitting layer material for organic light-emitting devices.

Specifically, the heterocyclic compound represented by Formula 1 can be used as a light-emitting layer material of the organic material layer of an organic light-emitting device, and in particular, it can be used as an n-type host material of the light-emitting layer. The heterocyclic compound represented by Formula 1 has fluorene as its basic skeleton and has a substituent with electron transfer properties.

In the heterocyclic compound represented by Formula 1, the electron transport ability and hole blocking ability can be adjusted by substituting a substituent with electron transport properties at an appropriate position, thereby lowering the driving voltage of the device and improving light efficiency. In addition, by bonding the remaining substituent among the two substituents to a specific position, the hole characteristics are strengthened and the thermal stability of the compound is improved by increasing the planarity and glass transition temperature of the azine derivative, thereby improving the lifespan characteristics of the device. There is.

Meanwhile, the heterocyclic compound represented by Formula 1 may further include the compound represented by Formula 2 as a p-type host material of the light-emitting layer, and can be applied to an organic light-emitting device in a combination of the two types. . In this case, due to the exciplex phenomenon, holes are injected into the p-type host and electrons are injected into the p-type (n-type) host. The ratio of the two types of compounds is By appropriately adjusting, the charge balance within the organic light emitting device can be balanced.

That is, when it contains the heterocyclic compound represented by Formula 1 or a combination of the heterocyclic compound of Formula 1 and the compound of Formula 2, the driving voltage, efficiency, and lifespan of the organic light-emitting device are improved.

1 to 3 are diagrams schematically showing the stacked structure of an organic light-emitting device according to an exemplary embodiment of the present application.

Hereinafter, this specification will be described in more detail.

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.

In this specification, the chemical formula means the position where it is combined.

In this specification, n in Cn refers to the number of carbon atoms. That is, for example, C6 to C60 means 6 to 60 carbon atoms.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.

In this specification, “substituted or unsubstituted” means deuterium; halogen group; -CN; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; Aryloxy group of C6 to C60; C1 to C60 alkylthioxy group; Arylthioxy group of C6 to C60; C1 to C60 alkyl sulfoxy group; C6 to C60 aryl sulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; Aryl group of C6 to C60; C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; means that one or more substituents selected from the group consisting of -NRR', or two or more substituents selected from the above exemplified substituents are substituted or unsubstituted with a connected substituent; , R, R' and R" are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; and a substituent consisting of at least one of a heteroaryl group.

In this specification, “when a substituent is not indicated in the chemical formula or compound structure” means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( ^2H , Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In an exemplary embodiment of the present application, “when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that can appear as substituents are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the content of deuterium may be 0% to 100%.

In an exemplary embodiment of the present application, in “cases where substituents are not indicated in the chemical formula or compound structure,” the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen, etc., explicitly excluding deuterium. Otherwise, hydrogen and deuterium can be used together in compounds.

In an exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element that has a deuteron consisting of one proton and one neutron as its nucleus. Hydrogen- It can be expressed as 2, and the element symbol can also be written as D or ² H.

In an exemplary embodiment of the present application, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A). Isotopes have the same number of protons but do not contain neutrons. It can also be interpreted as an element with a different number of neutrons.

In an exemplary embodiment of the present application, the meaning of the content T% of a specific substituent means that the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2. It can be defined as /T1Х100 = T%.

That is, in one example, The deuterium content of 20% in the phenyl group represented by means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuteriums among them is 1 (T2 in the formula), it will be expressed as 20%. You can. That is, the deuterium content of 20% in the phenyl group can be expressed by the following structural formula.

Additionally, in an exemplary embodiment of the present application, “a phenyl group with a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.

In this specification, halogen may be fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group Tyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methyl Examples include pentyl group, 4-methylhexyl group, and 5-methylhexyl group, but are not limited thereto.

In the present specification, the alkenyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited to these.

In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.

In this specification, a haloalkyl group refers to an alkyl group substituted with a halogen group, and specific examples include -CF ₃ and -CF ₂ CF ₃ , but are not limited thereto.

In this specification, the alkoxy group is represented by -O(R101), and examples of the above-described alkyl group may be applied to R101.

In the present specification, the aryloxy group is represented by -O(R102), and examples of the above-described aryl groups may be applied to R102.

In this specification, the alkylthioxy group is represented by -S(R103), and examples of the alkyl groups described above may be applied to R103.

In the present specification, the arylthioxy group is represented by -S(R104), and examples of the above-described aryl groups may be applied to R104.

In the present specification, the alkyl sulfoxy group is represented by -S(=0) ₂ (R105), and examples of the above-described alkyl groups may be applied to R105.

In the present specification, the arylsulfoxy group is represented by -S(=0) ₂ (R106), and examples of the above-described aryl groups may be applied to R106.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms and may be further substituted by another substituent. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 , 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.

In the present specification, the heterocycloalkyl group contains O, S, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the aryl group include phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, and phenalenyl group. , pyrenyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, these Condensation ring groups, etc. may be included, but are not limited thereto.

In the present specification, the terphenyl group may be selected from the following structures.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

When the fluorenyl group is substituted, , , , , , It may be, but is not limited to this.

In the present specification, the heteroaryl group contains S, O, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, or aryl group. The carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridine group, pyrrole group, pyrimidine group, pyridazine group, furan group, thiophene group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, furazine group, oxadiazole group, thiadiazole group, dithiazole group, tetrazolyl group, pyran group, thiopyran group, diazine group, oxazine group, thiazine group, dioxine group, triazine group, tetrazine group, quinoline group, Isoquinoline group, quinazoline group, isoquinazoline group, quinozoline group, naphthyridine group, acridine group, phenanthridine group, imidazopyridine group, diazanaphthalene group, triazindene group, indole group, indolizine group, Benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzo Sylol group, spirobi (dibenzosilol), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo [2,3-a] carbazole group, indolo [2,3-b] carbazole group, Indoline group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazole group, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5, 10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1, Examples include, but are not limited to, 2-a]imidazo[1,2-e]indoline group and 5,11-dihydroindeno[1,2-b]carbazole group.

In this specification, when the substituent is a carbazole group, it means bonding with the nitrogen or carbon of carbazole.

In this specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

In the present specification, the benzocarbazole group may have any one of the following structures.

In the present specification, the dibenzocarbazole group may have any one of the following structures.

In the present specification, the naphthobenzofuran group may have any of the following structures.

In the present specification, the naphthobenzothiophene group may have any one of the following structures.

In the present specification, the silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specific examples of silyl groups include: (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), etc., but is not limited thereto.

In the present specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specifically, it may be substituted with an alkyl group or an aryl group, and the examples described above may be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, dimethylphosphine oxide, diphenylphosphine oxide, and dinaphthylphosphine oxide.

In this specification, the amine group is represented by -N(R112)(R113), and R112 and R113 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. The amine group is -NH ₂ ; Monoalkylamine group; monoarylamine group; Monoheteroarylamine group; dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenyl fluorescein Examples include a nylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group, but are not limited to these.

In the present specification, the examples of the aryl group described above may be applied, except that the arylene group is a divalent group.

In the present specification, the examples of the heteroaryl group described above may be applied, except that the heteroarylene group is a divalent group.

As used herein, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.

Hydrocarbon rings and heterocycles that can be formed by adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and the rings are each of the above-described cycloalkyl groups and aryl groups, except that they are not monovalent. Structures exemplified by groups, heterocycloalkyl groups, and heteroaryl groups can be applied.

In an exemplary embodiment of the present application, a heterocyclic compound represented by Formula 1 is provided.

In an exemplary embodiment of the present application, a group not indicated as a substituent; Alternatively, it may mean that all groups represented by hydrogen can be replaced by deuterium. i.e. hydrogen; Alternatively, it may indicate that deuterium can be substituted for each other.

In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound represented by Formula 1 may be 0% to 100%.

In general, compounds bonded with hydrogen and compounds substituted with deuterium show differences in thermodynamic behavior. This is because the mass of a deuterium atom is twice that of hydrogen, but due to the difference in the masses of the atoms, deuterium has the characteristic of having lower vibration energy. Additionally, the bond length between carbon and deuterium is shorter than that with hydrogen, and the dissociation energy used to break the bond is also stronger. This is because the van der Waals radius of deuterium is smaller than that of hydrogen, making the stretching amplitude of the carbon-deuterium bond narrower.

Among the heterocyclic compounds represented by Formula 1 of the present invention, compounds substituted with deuterium have a lower ground state energy compared to compounds substituted with hydrogen, and as the bond length between carbon and deuterium becomes shorter, the molecular center becomes shorter. The volume (Molecular hardcore volume) decreases. As a result, electrical polarizability can be reduced and the volume of the device thin film can be increased by making intermolecular interaction weaker. These characteristics create an amorphous state in the thin film, leading to the effect of lowering the degree of crystallinity. Therefore, among the heterocyclic compounds represented by Formula 1, compounds substituted with deuterium can be effective in improving the heat resistance of OLED (Organic Light Emitting Diodes) devices, thereby improving their lifespan and driving characteristics.

In this specification, the 'OLED device' may be expressed by terms such as 'organic light emitting diode', 'OLED (Organic Light Emitting Diodes)', 'organic light emitting device', and 'organic electroluminescent device'.

In an exemplary embodiment of the present application, Et of Formula 1 may be a substituted or unsubstituted heteroaryl group containing N of C2 to C60.

In another embodiment, Et may be a substituted or unsubstituted heteroaryl group containing N of C2 to C40.

In another embodiment, Et may be a substituted or unsubstituted heteroaryl group containing N of C2 to C20.

In another embodiment, the Et is a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted phenanthroline group, or a substituted or unsubstituted group. It may be benzofuropyrimidine or substituted or unsubstituted benzothienopyrimidine.

In an exemplary embodiment of the present application, Ar1 of Formula 1 is a substituted or unsubstituted aryl group of C6 to C60; A substituted or unsubstituted C5 to C60 polycyclic heteroaryl group; Or, it may be a substituted or unsubstituted amine group.

In another embodiment, Ar1 is a substituted or unsubstituted aryl group of C6 to C40; A substituted or unsubstituted C5 to C40 polycyclic heteroaryl group; Or, it may be a substituted or unsubstituted amine group.

In another embodiment, Ar1 is a substituted or unsubstituted C6 to C20 aryl group; A substituted or unsubstituted C5 to C20 polycyclic heteroaryl group; Or, it may be a substituted or unsubstituted amine group.

In another embodiment, Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Alternatively, it may be an amine group substituted or unsubstituted by an aryl group.

In another embodiment, Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Alternatively, it may be an amine group substituted or unsubstituted by a phenyl group, biphenyl group, or dimethylfluorene group.

In an exemplary embodiment of the present application, p in Formula 1 is an integer of 1 to 4, and when p is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, p is 1. In an exemplary embodiment of the present application, p is 2. In an exemplary embodiment of the present application, p is 3. In an exemplary embodiment of the present application, p is 4. That is, when p is 2 or more, Ar1 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, L1 and L2 of Formula 1 are the same as or different from each other, and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C60 arylene group.

In another exemplary embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C40 arylene group.

In another exemplary embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C20 arylene group.

In another exemplary embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or it may be a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present application, m and n in Formula 1 are integers from 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same or different from each other.

In an exemplary embodiment of the present application, m is 0. In an exemplary embodiment of the present application, m is 1. In an exemplary embodiment of the present application, m is 2. In an exemplary embodiment of the present application, m is 3. That is, when m is 2 or more, L1 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, n is 0. In an exemplary embodiment of the present application, n is 1. In an exemplary embodiment of the present application, n is 2. In an exemplary embodiment of the present application, n is 3. That is, when n is 2 or more, L2 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, R1 to R8 in Formula 1 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forms a ring, and R, R' and R" are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C40 alkyl group; Substituted or unsubstituted C2 to C40 alkenyl group; Substituted or unsubstituted C2 to C40 alkynyl group; Substituted or unsubstituted C1 to C40 alkoxy group; Substituted or unsubstituted C3 to C40 cycloalkyl group; Substituted or unsubstituted C2 to C40 heterocycloalkyl group; Substituted or unsubstituted C6 to C40 aryl group; Substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C40 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 aliphatic or aromatic hetero ring. A ring can be formed.

In another exemplary embodiment, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; Substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aliphatic or aromatic hetero ring. A ring can be formed.

In another exemplary embodiment, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aryl group. It may form an aliphatic or aromatic heterocycle.

In an exemplary embodiment of the present application, two or more groups adjacent to each other among R1 to R3 are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle.

In another embodiment, two or more groups adjacent to each other among R1 to R3 are bonded to each other to form a substituted or unsubstituted C6 to C40 aliphatic or aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C40 aliphatic or aromatic heterocycle.

In another embodiment, two or more groups adjacent to each other among R1 to R3 are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C20 aliphatic or aromatic heterocycle.

In another embodiment, two or more groups adjacent to each other among R1 to R3 are bonded to each other to form a substituted or unsubstituted C6 to C10 aliphatic or aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C10 aliphatic or aromatic hetero ring.

In an exemplary embodiment of the present application, R7 and R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aryl group. It may form an aliphatic or aromatic heterocycle.

In another embodiment, R7 and R8 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C20 alkyl group; Alternatively, it may be a substituted or unsubstituted C6 to C20 aryl group, or may be combined with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.

In another exemplary embodiment, R7 and R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; and substituted or unsubstituted phenyl groups, or two or more groups adjacent to each other may be combined with each other to form substituted or unsubstituted fluorene.

In an exemplary embodiment of the present application, Formula 1 may be represented by the following Formula 1-A or Formula 1-B.

[Formula 1-A]

[Formula 1-B]

In Formula 1-A and Formula 1-B,

The definitions of Et, Ar1, L1, L2, m, n and p are the same as in Formula 1,

R1, R3 to R8, R11 and R12 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

a and b are integers from 0 to 4, and when a and b are each 2 or more, the substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, R1, R3 to R8, R11, and R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. A ring can be formed.

In another embodiment, R1, R3 to R8, R11, and R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C40 alkyl group; Substituted or unsubstituted C2 to C40 alkenyl group; Substituted or unsubstituted C2 to C40 alkynyl group; Substituted or unsubstituted C1 to C40 alkoxy group; Substituted or unsubstituted C3 to C40 cycloalkyl group; Substituted or unsubstituted C2 to C40 heterocycloalkyl group; Substituted or unsubstituted C6 to C40 aryl group; Substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C40 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 aliphatic or aromatic hetero ring. A ring can be formed.

In another embodiment, R1, R3 to R8, R11, and R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; Substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; Substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aliphatic or aromatic hetero ring. A ring can be formed.

In another embodiment, R1, R3 to R8, R11, and R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aryl group. It may form an aliphatic or aromatic heterocycle.

In an exemplary embodiment of the present application, a and b are integers from 0 to 4, and when a and b are each 2 or more, the substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, a is 0, 1, 2, 3, or 4, and when a is 2 or more, R11 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, b is 0, 1, 2, 3, or 4, and when b is 2 or more, R12 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

The definitions of Ar1, L1, L2, R1 to R8, m, n and p are the same as in Formula 1,

X1 to X5 are the same or different from each other, and are each independently N; or CRx, and at least one is N,

Y1 is O; or S,

Rx, R13 and R14 are hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group,

c is an integer from 0 to 7, d is an integer from 0 to 5, and when c and d are each 2 or more, the substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, X1 to X5 are the same as or different from each other, and are each independently N; or CRx, and at least one may be N.

In another embodiment, one of X1 to X5 may be N, and the others may be CRx.

In another embodiment, two of X1 to X5 may be N, and the remainder may be CRx.

In another embodiment, three of X1 to X5 may be N, and the remainder may be CRx.

In an exemplary embodiment of the present application, Y1 is O; Or it may be S.

In another exemplary embodiment, Y1 may be O.

In another exemplary embodiment, Y1 may be S.

In an exemplary embodiment of the present application, Rx, R13 and R14 are hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

In another exemplary embodiment, Rx, R13, and R14 are hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzothiophene group; Or it may be a substituted or unsubstituted dibentofuran group.

In an exemplary embodiment of the present application, -Ar1 of Formula 1 may be represented by any one of the structures 1a to 1d below.

[Structure 1a]

[Structure 1b]

[Structure 1c]

[Structure 1d]

In structures 1a to 1d,

Ar11 is a substituted or unsubstituted aryl group of C6 to C20,

Y2 is O; or S,

R15, R16, Ar12 and Ar13 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

e is an integer from 0 to 7, f is an integer from 0 to 8, and when e and f are each 2 or more, the substituents in parentheses are the same or different from each other,

p1 to p3 are each an integer of 1 to 4, and when p1 to p3 are each 2 or more, the substituents in the parentheses are the same or different from each other,

는 상기 화학식 1의 L1에 연결되는 위치이다.

is a position connected to L1 of Formula 1 above.

In an exemplary embodiment of the present application, Formula 1 may be represented by any one of the following Formulas 1-4 to 1-7.

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Formulas 1-4 to 1-7,

The definitions of Et, L1, L2, R1 to R8, m and n are the same as in Formula 1,

Ar11 is a substituted or unsubstituted aryl group of C6 to C20,

Y2 is O; or S,

R15, R16, Ar12 and Ar13 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

e is an integer from 0 to 7, f is an integer from 0 to 8, and when e and f are each 2 or more, the substituents in parentheses are the same or different from each other,

p1 to p3 are each an integer of 1 to 4, and when p1 to p3 are each 2 or more, the substituents in the parentheses are the same or different from each other.

In an exemplary embodiment of the present application, Ar11 may be a substituted or unsubstituted C6 to C20 aryl group.

In another exemplary embodiment, Ar11 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted terphenyl group; Or it may be a substituted or unsubstituted triphenylene group.

In an exemplary embodiment of the present application, p1 in Formula 1 is an integer of 1 to 4, and when p1 is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, p1 is 1. In an exemplary embodiment of the present application, p1 is 2. In an exemplary embodiment of the present application, p1 is 3. In an exemplary embodiment of the present application, p1 is 4. That is, when p1 is 2 or more, Ar11 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, Y2 is O; Or it may be S.

In another exemplary embodiment, Y2 may be O.

In another exemplary embodiment, Y2 may be S.

In an exemplary embodiment of the present application, R15, R16, Ar12, and Ar13 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. A ring can be formed.

In another embodiment, R15, R16, Ar12, and Ar13 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C40 alkyl group; Substituted or unsubstituted C2 to C40 alkenyl group; Substituted or unsubstituted C2 to C40 alkynyl group; Substituted or unsubstituted C1 to C40 alkoxy group; Substituted or unsubstituted C3 to C40 cycloalkyl group; Substituted or unsubstituted C2 to C40 heterocycloalkyl group; Substituted or unsubstituted C6 to C40 aryl group; Substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C40 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 aliphatic or aromatic hetero ring. A ring can be formed.

In another embodiment, R15, R16, Ar12, and Ar13 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; Substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aliphatic or aromatic hetero ring. A ring can be formed.

In another embodiment, R15, R16, Ar12, and Ar13 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; and a substituted or unsubstituted C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aryl group. It may form an aliphatic or aromatic heterocycle.

In an exemplary embodiment of the present application, p2 is an integer of 1 to 4, and when p2 is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, p2 is 1. In an exemplary embodiment of the present application, p2 is 2. In an exemplary embodiment of the present application, p2 is 3. In an exemplary embodiment of the present application, p2 is 4. That is, when p2 is 2 or more, Ar12 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, p3 is an integer of 1 to 4, and when p3 is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, p3 is 1. In an exemplary embodiment of the present application, p3 is 2. In an exemplary embodiment of the present application, p3 is 3. In an exemplary embodiment of the present application, p3 is 4. That is, when p3 is 2 or more, Ar13 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, e is 0, 1, 2, 3, 4, 5, 6, or 7, and when e is 2 or more, R15 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, f is 0, 1, 2, 3, 4, 5, 6, 7, or 8, and when f is 2 or more, R16 in parentheses are the same or different.

In an exemplary embodiment of the present application, Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

Additionally, by introducing various substituents into the structure of Formula 1, a compound having the unique properties of the introduced substituent can be synthesized. For example, by introducing substituents mainly used in hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials used in the manufacture of organic light-emitting devices into the core structure, a material that satisfies the conditions required for each organic layer can be created. It can be synthesized.

In addition, the compound of Formula 1 has excellent thermal stability, and this thermal stability provides driving stability to the organic light-emitting device and improves lifespan characteristics.

In an exemplary embodiment of the present application, a first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a heterocyclic compound represented by Formula 1. provides.

In another exemplary embodiment, a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes one type of heterocyclic compound represented by Formula 1. A light emitting device is provided.

In another exemplary embodiment, a first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes two or more types of heterocyclic compounds represented by Formula 1. An organic light emitting device is provided.

In another embodiment, the heterocyclic compound represented by Formula 1 may be used as a light-emitting material for the light-emitting layer of an organic light-emitting device.

In another embodiment, the heterocyclic compound represented by Formula 1 may be used as a light-emitting material for the light-emitting layer of an organic light-emitting device and may be used as an n-type host material.

In an exemplary embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

In another exemplary embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the blue organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the green organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the red organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

In an exemplary embodiment of the present application, specific details about the heterocyclic compound represented by Formula 1 are the same as those described above.

The organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the heterocyclic compound described above.

The heterocyclic compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include a smaller number of organic material layers.

In an exemplary embodiment of the present application, Ir(ppy) ₃ , a green phosphorescent dopant, may be used as the iridium-based dopant.

In an exemplary embodiment of the present application, (piq) ₂ (Ir) (acac), a red phosphorescent dopant, may be used as the iridium-based dopant.

In an exemplary embodiment of the present application, an organic light-emitting device is provided wherein the organic material layer of the organic light-emitting device includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

In an exemplary embodiment of the present application, an organic light-emitting device is provided wherein the organic material layer of the organic light-emitting device includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound.

In the organic light emitting device of the present invention, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer includes an electron transport layer, a light emitting layer, or a hole blocking layer, and the electron transport layer, the light emitting layer, or the hole blocking layer may include the heterocyclic compound.

In the organic light emitting device of the present application, materials with a relatively high work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

As the cathode material, materials with a relatively low work function can be used, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

As the hole injection material, known hole injection materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994). Starburst type amine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid, a soluble conductive polymer, or poly( 3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate), Polyaniline/Camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) can be used.

As hole transport materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular or high molecular materials may also be used.

Electron transport materials include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular substances but also high molecular substances may be used.

For example, LiF is typically used as an electron injection material in the industry, but the present application is not limited thereto.

Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed. At this time, two or more light emitting materials can be deposited and used from individual sources, or they can be premixed and deposited from a single source. Additionally, a fluorescent material can be used as a light-emitting material, but it can also be used as a phosphorescent material. As a light-emitting material, a material that emits light by combining holes and electrons injected from an anode and a cathode, respectively, may be used, but materials that participate in light emission together with a host material and a dopant material may also be used.

When using a mixture of hosts of a light emitting material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more types of materials, such as an n-type host material or a p-type host material, can be selected and used as a host material for the light emitting layer.

The organic light emitting device according to an exemplary embodiment of the present application may be a front emitting type, a rear emitting type, or a double-sided emitting type depending on the material used.

The heterocyclic compound according to an exemplary embodiment of the present application may function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

The organic light emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

1 to 3 illustrate the stacking order of electrodes and organic material layers of an organic light-emitting device according to an exemplary embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and structures of organic light-emitting devices known in the art may also be applied to the present application.

According to Figure 1, an organic light emitting device is shown in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, it is not limited to this structure, and an organic light-emitting device may be implemented in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG. 2.

Figure 3 illustrates the case where the organic material layer is multi-layered. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited by this laminated structure, and if necessary, the remaining layers except the light-emitting layer may be omitted, and other necessary functional layers may be added.

In an exemplary embodiment of the present application, an organic light-emitting device is provided in which the organic material layer of the organic light-emitting device containing the heterocyclic compound represented by Formula 1 further includes a compound represented by Formula 2 below.

[Formula 2]

In Formula 2,

Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted heteroaryl group of C2 to C60, q and r are each integers of 1 to 4, and when q and r are each 2 or more, the substituents in parentheses are the same or different from each other,

L3 is a direct bond; Substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted heteroarylene group of C2 to C60, o is each an integer of 0 to 3, and when o is 2 or more, the substituents in parentheses are the same or different from each other,

Ra and Rb are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group,

R9 and R10 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,

R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

g is an integer from 0 to 5, h is an integer from 0 to 4, and when g and h are each 2 or more, the substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, Ar2 and Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another embodiment, Ar2 and Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

In another embodiment, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted fluorene group; Or it may be a substituted or unsubstituted spirobifluorene group.

In another embodiment, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted dimethylfluorene group; Substituted or unsubstituted diphenylfluorene group; Or it may be a substituted or unsubstituted spirobifluorene group.

In an exemplary embodiment of the present application, q in Formula 2 is an integer of 1 to 4, and when q is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, q is 1. In an exemplary embodiment of the present application, q is 2. In an exemplary embodiment of the present application, q is 3. In an exemplary embodiment of the present application, q is 4. That is, when q is 2 or more, Ar2 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, r in Formula 2 is an integer of 1 to 4, and when r is 2 or more, the substituents in parentheses are the same or different from each other. In an exemplary embodiment of the present application, r is 1. In an exemplary embodiment of the present application, r is 2. In an exemplary embodiment of the present application, r is 3. In an exemplary embodiment of the present application, r is 4. That is, when r is 2 or more, Ar3 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, L3 is a direct bond; Substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.

In another embodiment, L3 is a direct bond; Substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.

In another embodiment, L3 is a direct bond; Substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C2 to C20 heteroarylene group.

In another embodiment, L3 is a direct bond; Substituted or unsubstituted C6 to C10 arylene group; Or it may be a substituted or unsubstituted C2 to C10 heteroarylene group.

In another embodiment, L3 is a direct bond; It may be a substituted or unsubstituted C6 to C10 arylene group.

In another embodiment, L3 is a direct bond; Substituted or unsubstituted phenylene group; Or it may be a substituted or unsubstituted naphthylene group.

In another embodiment, L3 is a direct bond; phenylene group; Or it may be a naphthylene group.

In an exemplary embodiment of the present application, o is each an integer from 0 to 3, and when o is 2 or more, the substituents in parentheses are the same or different from each other. In one embodiment of the present application, o is 0. In an exemplary embodiment of the present application, o is 1. In one embodiment of the present application, o is 2. In one embodiment of the present application, o is 3. That is, when o is 2 or more, L3 in parentheses are the same or different from each other.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; and a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present application, Ra and Rb are the same or different from each other, and are each independently a substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted C6 to C20 aryl group.

In an exemplary embodiment of the present application, R9 and R10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. A ring can be formed.

In another exemplary embodiment, R9 and R10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C40 alkyl group; Substituted or unsubstituted C2 to C40 alkenyl group; Substituted or unsubstituted C2 to C40 alkynyl group; Substituted or unsubstituted C1 to C40 alkoxy group; Substituted or unsubstituted C3 to C40 cycloalkyl group; Substituted or unsubstituted C2 to C40 heterocycloalkyl group; Substituted or unsubstituted C6 to C40 aryl group; Substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C40 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 aliphatic or aromatic hetero ring. A ring can be formed.

In another exemplary embodiment, R9 and R10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; Substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aliphatic or aromatic hetero ring. A ring can be formed.

In another embodiment, R9 and R10 are the same as or different from each other, and are each independently hydrogen; Or it may be deuterium.

In another exemplary embodiment, R9 and R10 may be hydrogen.

In another embodiment, R9 and R10 may be deuterium.

In an exemplary embodiment of the present application, g is 0, 1, 2, 3, 4, or 5, and when g is 2 or more, R9 in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, h is 0, 1, 2, 3, or 4, and when each h is 2 or more, R10 in parentheses are the same or different from each other.

In one embodiment of the present invention, Formula 2 provides an organic light-emitting device represented by any one of the following compounds, but is not limited thereto.

The organic light-emitting device further containing the compound represented by Formula 2 may be applied to the organic light-emitting device containing the heterocyclic compound represented by Formula 1 described above.

In another embodiment, the compound represented by Formula 2 may be used as a light-emitting material for the light-emitting layer of an organic light-emitting device.

In another embodiment, the compound represented by Formula 2 may be used as a light-emitting material of the light-emitting layer of an organic light-emitting device and may be used as a p-type host material.

In the organic light emitting device of the present invention, the organic material layer may include a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2. The organic material layer can be formed by pre-mixing the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 using a thermal vacuum deposition method.

In another organic light-emitting device, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2.

In another organic light emitting device, the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material may include a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2. .

In another organic light emitting device, the organic material layer includes a light emitting layer, the n-type host material of the light emitting layer includes a heterocyclic compound represented by Formula 1, and the p-type host material includes a compound represented by Formula 2. may include.

In one embodiment of the present application, preparing a substrate; forming a first electrode on the substrate; Forming one or more organic layers on the first electrode; And forming a second electrode on the organic layer, wherein the forming the organic layer includes forming one or more organic layers using a composition for an organic layer according to an exemplary embodiment of the present application. A method for manufacturing an organic light emitting device is provided.

In an exemplary embodiment of the present application, the step of forming the organic material layer is performed by supplying the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 to each individual source, and then using a thermal vacuum deposition method. A method of manufacturing an organic light emitting device is provided.

In an exemplary embodiment of the present application, the step of forming the organic material layer is formed by pre-mixing the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 using a thermal vacuum deposition method. A method for manufacturing an organic light emitting device is provided.

The organic light-emitting device according to an exemplary embodiment of the present application can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the above-described compound.

The organic light emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer. You can.

In an exemplary embodiment of the present application, a composition for an organic material layer of an organic light-emitting device comprising a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2 is provided.

The weight ratio of the heterocyclic compound represented by Formula 1 to the compound represented by Formula 2 in the composition may be 1:10 to 10:1, 1:8 to 8:1, and 1:5 to 5. : 1, and 1 : 2 to 2 : 1, but is not limited thereto.

The composition can be used when forming an organic material layer of an organic light-emitting device, and can be particularly preferably used as a host material for the light-emitting layer.

The composition is a simple mixture of two or more compounds, and powdered materials may be mixed before forming the organic material layer of the organic light-emitting device, or compounds in a liquid state at an appropriate temperature or higher may be mixed. The composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.

The composition may further include materials known in the art, such as solvents and additives.

Below, the present specification is described in more detail through examples, but these are only for illustrating the present application and are not intended to limit the scope of the present application.

<Example>

[Preparation Example 1] Preparation of Compound 2

1) Preparation of compound 2-2

2-bromo-3-iodonaphthalene (A) (20g, 0.060mol, 1eq), phenylboronic acid (B) (8g, 0.066mol, 1.1eq) , K ₃ PO ₄ (38g, 0.18mol, 3eq), Pd(PPh ₃ ) ₄ (3.4g, 0.003mol, 0.05eq) with 1,4-dioxane (400ml) and H ₂ O (100ml) was added and stirred at 100°C for 6 hours. After the reaction was terminated by adding water, extraction was performed using methylene chloride (MC) and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 15 g of compound 2-2 was obtained with a yield of 88%.

2) Preparation of compound 2-3

Compound 2-2 (15g, 0.053mol, 1eq), 4-chloro-2-(methoxycarbonyl)phenyl)boronic acid (12.5g, 0.058mol) , 1.1eq), K ₃ PO ₄ (33.7g, 0.159mol, 3eq), Pd(PPh ₃ ) ₄ (3g, 0.003mol, 0.0026eq) and 1,4-dioxane (300ml) ) and H ₂ O (750ml) were added and stirred at 100°C for 6 hours. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 15 g of compound 2-3 was obtained with a yield of 76%.

3) Preparation of Compound 2-4

Compound 2-3 (15g, 0.040mol, 1eq) was dissolved in tetrahydrofuran (150ml), and then methylmagnesium bromide was dissolved in ether at 0°C (molarity: 3M) (D) ) (40ml, 0.120 mol, 3eq) was slowly added and stirred at 60°C for 6 hours. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . Boron trifluoride diethyl etherate was added to the reactant dissolved in MC, and then stirred at room temperature (RT) for 4 hours. After separation using a silica gel column, 10 g of compound 2-4 was obtained with a yield of 70%.

4) Preparation of Compound 2-5

Compound 2-4 (10g, 0.028mol, 1eq) 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxa borolane)4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11g, 0.042mol, 1.5eq), KOAc (8.3g, 0.084mol, 3eq), Pd(dba) ₂ (0.8g, 0.001mol, 0.05eq), and P(Cy) ₃ (Tricyclohexylphosphine) (0.8g, 0.003mol, 0.1 1,4-dioxane (150ml) was added to eq) and stirred at 100°C for 8 hours. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . By separation using a silica gel column, 9g of compound 2-5 was obtained with a yield of 72%.

5) Preparation of Compound 2

Compound 2-5 (9g, 0.020mol, 1eq), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2- ([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) (E) (7.3g, 0.021mol, 1.05eq), K ₂ CO ₃ ( 8.4g, 0.060mol, 3eq), Pd(PPh ₃ ) ₄ (0.9g, 0.001mol, 0.05eq) with 1,4-dioxane (90ml) and H ₂ O (30ml) Added and stirred at 100°C for 7 hours. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 8 g of compound 2 was obtained with a yield of 63%.

[Preparation Example 2] Preparation of compound 279-2

1) Preparation of compound 279-2

2-bromo-3-iodonaphthalene (A) (20g, 0.060mol, 1eq), 5H-benzo[b]carbazole (B') (14.4g, 0.066mol, 1.1 eq), NaOt-Bu (8.7g, 0.09mol, 1.5eq), _Pd2 (dba) ₃ (2.8g, 0.003mol, 0.05eq), XPhos (2.8g, 0.006mol, 0.1eq) in Xylene (200ml) was added and stirred at 150°C for 6 hours. After adding water to terminate the reaction, extraction was performed using MC (methylene chloride) and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 15 g of compound 279-2 was obtained with a yield of 59%.

In the preparation of Compound 2-3 of Preparation Example 1, Compound 2-3 to Compound 2-5 and Compound 2-5 of Preparation Example 1, except that Compound 279-2 was used instead of Compound 2-2. Compound 279 was prepared in the same manner as the preparation method of 2.

[Preparation Example 3] Preparation of compound 413-4

2) Preparation of compound 413-4

2-(2-bromo-4-chlorophenyl)-3-phenylnaphthalene (11g, 0.028mol, 1eq) was dissolved in anhydrous tetrahydrofuran. After dissolving in tetrahydrofuran (110ml), n-BuLi (12.3ml, 0.031mol, 1.1eq) was slowly added at -78°C. After 1 hour, 9H-fluoren-9-one (D') (6g, 0.034mol, 1.2eq) was slowly added and stirred at room temperature (RT) for 6 hours. After adding water to terminate the reaction, extraction was performed using MC (methylene chloride) and water. Afterwards, moisture was removed with MgSO ₄ . The water-removed reaction product was dissolved in toluene (100ml), trifluoromethanesulfonic acid (TfOH) (10ml) was added at 0°C, and stirred at 60°C for 2 hours. Afterwards, the temperature was lowered, water was added to terminate the reaction, and extraction was performed using MC (methylene chloride) and water. Afterwards, moisture was removed with MgSO ₄ . Afterwards, it was separated using a silica gel column to obtain 7g of compound 413-4 with a yield of 53%.

In the preparation of compound 2-4 of Preparation Example 1, compounds 2-3 to 2-5 and compounds of Preparation Example 1 were used, except that Compound 413-3 was used instead of Compound 2-3. Compound 413 was prepared in the same manner as the preparation method of 2.

In Preparation Example 1, 2-bromo-3-iodonaphthalene (A), phenylboronic acid (B), methylmagnesium bromide (D) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-4- In the same manner as Preparation Example 1, except that intermediates A, B, C, D and E of Table 1 below were used instead of yl)-4-chloro-6-phenyl-1,3,5-triazine) (E) The compounds shown in Table 1 below were synthesized.

[Preparation Example 4] Preparation of compound 487

Compound 325 prepared in Preparation Example 1 (8g, 0.011mol, 1eq), Triflic acid (TfOH) _{(2.4g, 0.016mol, 1.5eq), and D 6 -Benzene} (80ml) was added and stirred at 100°C for 8 hours. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 7 g of compound 487 was obtained with a yield of 83%.

Compounds were prepared as in Preparation Examples 1 to 3, and the synthesis confirmation results are shown in Tables 2 and 3. Table 2 shows the measured values of 1H NMR (CDCl ₃ , 200Mz), and Table 3 shows the measured values of FD-MS (Field desorption mass spectrometry).

[Experimental Example 1] Production of organic light-emitting device

A glass substrate coated with a thin film of indium tinoxide (ITO) with a thickness of 1,500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, it was ultrasonic washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and treated with UV (Ultraviolet Ozone) for 5 minutes using UV light in a UV (Ultraviolet) cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

A common layer on the ITO transparent electrode (anode), a hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB(N,N'-Di (1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was deposited with a compound listed in Table 4 as a red host, and (piq) ₂ (Ir) (acac) was used as a red phosphorescent dopant, and 3 wt% of the Ir compound was doped into the host and deposited at 400 Å.

Afterwards, 30Å of Bphen was deposited as a hole blocking layer, and 250Å of Alq ₃ was deposited on top of it as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and an aluminum (Al) cathode was deposited to a thickness of 1,200Å to form the cathode on the electron injection layer, thereby forming an organic An electroluminescent device was manufactured.

Meanwhile, all organic compounds required for OLED device production were purified by vacuum sublimation under 10 ^-8 to 10 ^-6 torr for each material and used for OLED production.

The electroluminescence (EL) characteristics of the organic electroluminescent devices manufactured as described above (Examples 1 to 32 and Comparative Examples 1 to 13) were measured using M7000 from McScience, and the measurement results were used to obtain T90 was measured when the standard luminance was 6,000 cd/m ² using a lifespan measurement equipment (M6000). The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 4 below.

Comparative compounds H1 to H13 used in the comparative examples of Table 4 are as follows.

As can be seen from the results in Table 4, it was confirmed that the organic light emitting device using the host material of the present invention had a lower driving voltage and improved luminous efficiency and lifespan compared to the comparative example.

When a heterocyclic compound with a substituent with electron transport properties is substituted at an appropriate position, compared to the case where a compound substituted at a different position is used, the hole blocking phenomenon occurring in the dopant is eliminated and pi-pi stacking of the aromatic ring ( Improves device stability by suppressing pi-pi stacking. Therefore, by preventing the phenomenon of deterioration of the characteristics of the device, it appears that the device using the compound of the present invention showed superior results in all aspects of driving voltage, luminous efficiency, and lifespan than the device using the comparative example compound.

[Experimental Example 2] Production of organic light-emitting device

A glass substrate coated with a thin film of indium tinoxide (ITO) with a thickness of 1,500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and treated with UV (Ultraviolet Ozone) for 5 minutes using UV light in a UV (Ultraviolet) cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

A common layer on the ITO transparent electrode (anode), a hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine), a hole transport layer NPB(N,N'-Di (1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) is used as an electron blocking layer TAPC (cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine]). formed.

A light emitting layer was thermally vacuum deposited thereon as follows. For the light-emitting layer, two types of compounds listed in Table 5 below were deposited from one source as a red host, and (piq) ₂ (Ir) (acac) was used as a red phosphorescent dopant, and 3 wt% of the Ir compound was doped into the host to form a layer of 400 Å. deposited. The ratios shown in Table 5 below are the weight ratios of each compound.

Afterwards, 30Å of Bphen was deposited as a hole blocking layer, and 250Å of TPBI was deposited on top of it as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and an aluminum (Al) cathode was deposited to a thickness of 1,200 Å to form a cathode on the electron injection layer, thereby maintaining the organic electric field. A light emitting device was manufactured.

Meanwhile, all organic compounds required for OLED device production were purified by vacuum sublimation under 10 ^-8 to 10 ^-6 torr for each material and used for OLED production.

The electroluminescence (EL) characteristics of the organic electroluminescent devices manufactured as described above (Examples 33 to 66 and Comparative Examples 14 to 26) were measured using M7000 from McScience. T90 was measured when the standard luminance was 6,000 cd/m ² using a lifespan measurement equipment (M6000). Table 5 shows the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention.

Comparative compounds H1 to H13 used in the comparative examples in Table 5 are the same as the compounds described in Table 4.

As can be seen from the results in Table 5, when the heterocyclic compound represented by Formula 1 of the present invention is used as an N-type host and the compound represented by Formula 2 is mixed with a P-type host and deposited, organic light emission It was confirmed that the driving voltage, luminous efficiency, and lifespan of the device were improved. When a donor (p-type host) with good hole transport ability and an acceptor (n-type host) with good electron transport ability are used together as hosts for an emitting layer, the exciplex phenomenon of the N+P compound occurs.

Accordingly, since holes are injected into the p-type host and electrons are injected into the n-type host, charge balance within the device can be maintained. In other words, it can be seen that combining an N-type host compound with appropriate electron transport properties and a P-type host compound with appropriate hole transport characteristics in an appropriate ratio can help improve driving voltage, luminous efficiency, and lifespan. there was.

100: substrate
200: anode
300: Organic layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (15)

Heterocyclic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Et is a substituted or unsubstituted heteroaryl group containing N of C2 to C60,
Ar1 is a substituted or unsubstituted aryl group of C6 to C60; A substituted or unsubstituted C5 to C60 polycyclic heteroaryl group; or a substituted or unsubstituted amine group, p is an integer of 1 to 4, and when p is 2 or more, the substituents in parentheses are the same or different from each other,
L1 and L2 are the same or different from each other and are each independently directly bonded; or a substituted or unsubstituted C6 to C60 arylene group, m and n are each an integer of 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same or different from each other,
R1 to R8 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,
R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A substituted or unsubstituted C2 to C60 heteroaryl group,
Two or more groups among R1 to R3 that are adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Or, it forms a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by Formula 1-A or Formula 1-B:
[Formula 1-A]

[Formula 1-B]

In Formula 1-A and Formula 1-B,
The definitions of Et, Ar1, L1, L2, m, n and p are the same as in Formula 1,
R1, R3 to R8, R11 and R12 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,
R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
a and b are integers from 0 to 4, and when a and b are each 2 or more, the substituents in parentheses are the same or different from each other. The method according to claim 1, wherein the formula 1 is a heterocyclic compound represented by any one of the following formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
The definitions of Ar1, L1, L2, R1 to R8, m, n and p are the same as in Formula 1,
X1 to X5 are the same or different from each other, and are each independently N; or CRx, and at least one is N,
Y1 is O; or S,
Rx, R13 and R14 are hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group,
c is an integer from 0 to 7, d is an integer from 0 to 5, and when c and d are each 2 or more, the substituents in parentheses are the same or different from each other. The method according to claim 1, wherein the formula 1 is a heterocyclic compound represented by any one of the following formulas 1-4 to 1-7:
[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Formulas 1-4 to 1-7,
The definitions of Et, L1, L2, R1 to R8, m and n are the same as in Formula 1,
Ar11 is a substituted or unsubstituted aryl group of C6 to C20,
Y2 is O; or S,
R15, R16, Ar12 and Ar13 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,
R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
e is an integer from 0 to 7, f is an integer from 0 to 8, and when e and f are each 2 or more, the substituents in parentheses are the same or different from each other,
p1 to p3 are each an integer of 1 to 4, and when p1 to p3 are each 2 or more, the substituents in the parentheses are the same or different from each other. The method according to claim 1, wherein R7 and R8 are the same or different from each other, and are each independently a substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted C6 to C20 aryl group, or a heterocyclic compound that combines with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

























first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the heterocyclic compound according to any one of claims 1 to 6. Phosphorus organic light emitting device. The organic light-emitting device of claim 7, wherein the organic material layer further includes a compound represented by the following formula (2):
[Formula 2]

In Formula 2,
Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted heteroaryl group of C2 to C60, q and r are each integers of 1 to 4, and when q and r are each 2 or more, the substituents in parentheses are the same or different from each other,
L3 is a direct bond; Substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted heteroarylene group of C2 to C60, o is each an integer of 0 to 3, and when o is 2 or more, the substituents in parentheses are the same or different from each other,
Ra and Rb are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group,
R9 and R10 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,
R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
g is an integer from 0 to 5, h is an integer from 0 to 4, and when g and h are each 2 or more, the substituents in parentheses are the same or different from each other. The method of claim 8, wherein Ar2 and Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; Or an organic light-emitting device that is a substituted or unsubstituted C2 to C20 heteroaryl group. The organic light-emitting device according to claim 8, wherein Formula 2 is represented by any one of the following compounds:








The organic light-emitting device of claim 8, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2. The method of claim 8, wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes a compound represented by Formula 1 and a heterocyclic compound represented by Formula 2. device. The method of claim 8, wherein the organic light emitting device further comprises one or two layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Phosphorus organic light emitting device. A heterocyclic compound represented by formula 1 according to claim 1; and a composition for the organic material layer of an organic light-emitting device comprising a compound represented by the following formula (2):
[Formula 2]

In Formula 2,
Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted heteroaryl group of C2 to C60, q and r are each integers of 1 to 4, and when q and r are each 2 or more, the substituents in parentheses are the same or different from each other,
L3 is a direct bond; Substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted heteroarylene group of C2 to C60, o is each an integer of 0 to 3, and when o is 2 or more, the substituents in parentheses are the same or different from each other,
Ra and Rb are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group,
R9 and R10 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero ring. forming a ring,
R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or An unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
g is an integer from 0 to 5, h is an integer from 0 to 4, and when g and h are each 2 or more, the substituents in parentheses are the same or different from each other. In claim 14,
A composition for an organic material layer of an organic light-emitting device, wherein the weight ratio of the heterocyclic compound represented by Formula 1 to the compound represented by Formula 2 in the composition is 1:10 to 10:1.

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